


However You Like It

by jasmasson



Category: Supernatural
Genre: Community: reel_spn, Crossdressing, M/M
Language: English
Status: Completed
Published: 2007-08-22
Updated: 2007-08-22
Packaged: 2017-10-15 18:16:13
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 9,090
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/163541
Author URL: https://archiveofourown.org/users/jasmasson/pseuds/jasmasson
Summary: <blockquote class="userstuff">
              <p>Sam and Dean go undercover in dresses.  They appear to like it more than they thought they would.</p>
            </blockquote>





	However You Like It

**Author's Note:**

> **Author’s notes** : For the [](http://community.livejournal.com/reel_spn/profile)[**reel_spn**](http://community.livejournal.com/reel_spn/) challenge and very loosely based on [ Some Like it Hot](http://www.imdb.com/title/tt0053291/). So loosely, in fact, it isn’t even AU.  
>  **Spoilers** : Very vague for AHBL2 and Nightshifter.  
>  **Beta** : Thanks to the wonderful [](http://candygramme.livejournal.com/profile)[**candygramme**](http://candygramme.livejournal.com/).  
> 

***

“How could he have found us?” Dean grated out, as they sat in the car, pulled off into the woods.

Henricksen was at their motel. Sam was grateful that his visions had started working for him, for a change, and had given him a heads up that the FBI was staking out their rooms.

“We should have ditched the car,” Sam said, bluntly. “Changing the plates was never going to be enough.”

“Hey!” Dean elbowed him, sharply. “Don’t listen to him baby,” Dean crooned, stroking the Impala’s steering wheel. “I let you go over my dead body.”

Sam gritted his teeth, not reminding Dean that his visions were _death_ visions, and that Henricksen _really_ hated Dean. An ambush at a motel was the perfect venue for a stray bullet, and Sam wouldn’t soon forget the sight of his brother taking one to the chest right in front of him.

“We can’t go back to the motel,” Sam said, firmly.

“Yeah, thanks for that, genius,” Dean said, grimly. “Thank God we’ve got our bags. So we’ve still got Dad’s journal…”

And my laptop, Sam thought.

“… and the car.”

“I think,” Sam said, slowly, knowing perfectly well how this was going to be taken. “I think we’re really going to have to leave the car.”

“Forget it,” Dean said shortly.

“Dean, there’s only one road out of this town, and we need to get out _now_ before Henricksen realizes we’re not going back to the motel,” Sam reasoned. “He’s not stupid; he’ll have blocked the road both ways as a precaution. He’s not going to risk letting us escape.”

“He might not have,” Dean said, jaw set.

“He _will_ have. And, yes, probably just with the local cops, but any inter-agency rivalry aside, they’re going to notice the Impala.”

“She is noticeable,” Dean agreed, momentarily distracted and smiling smugly.

“ _Dean_! Focus. We _cannot_ get the Impala out of here. Even if we tried going cross country we’d kick up too much dirt and we’d be bound to be seen.”

Dean grimaced, probably at the mere thought of subjecting his baby to that.

“I’m not leaving her until I know for sure,” Dean said, stubbornly.

“Look, we’ll park _her_ in the woods out back behind Jefferson’s place,” they’d been to Jefferson’s ancient shack in the woods to salt and burn his remains for this job, and if anyone had been near there in the past 30 years, Sam would be very surprised, “and we’ll get Bobby to pick her up and meet us after Henricksen gives up.” Because, hey, the Impala was home to Sam, too, he just wasn’t a _crazy obsessive_ about her. It. Like some people.

“Why don’t we just wait it out at Jefferson’s place?” Dean said, brightening up.

“I’m not risking it,” Sam said, flatly. “I saw you die once today, and I’m not going to see it again any time soon.”

Sam put all his little brother pleading into his look at Dean. He’d just saved Dean from the crossroads Demon, and he _was not_ losing him to a human.

“Fuck,” Dean said and threw the Impala into gear, heading back to Jefferson’s. “Fine. We’ll walk into town, and if I don’t see a police roadblock we’re coming back and getting her, and you’re giving her a wax in apology for even making me _think_ about leaving her.”

***

Not that Sam wanted to wash the car, but he was as disappointed to see the roadblock as Dean.

“Fuck. I guess we’ll have to steal a car and try and get through that way.” It wasn’t ideal, but the cops wouldn’t be as invested in trying to apprehend Sam and Dean as Henricksen was; they looked kind of lazy – waving the traffic through. “Actually, we should steal two cars. We’d better split up, as well, because they’ll be looking for two guys together.” Sam glanced over the road to the barber’s shop and bit the bullet. “I’ll get my hair cut quickly.” He glanced over at Dean. “Maybe you could dye yours? Get some glasses, or something.” God, it was still very risky.

“We’re not splitting up, Sam. No way.”

“Just through the roadblock.”

“No.”

This argument wasn’t over, but for now…

“Let’s go to the barber’s. There’s one down the side street, so we’re not out in the open.”

Dean had a look on his face like he knew this wasn’t over either, but followed his brother.

“If I’d known this was what it’d take to make you get a haircut, Sammy, I’d have called Henricksen myself.”

“Fuck off,” Sam said, because, damn. He was actually kind of annoyed (okay _upset_ ) about having to cut his hair. But, really. What else could they do?

***

In the barber’s there was only one other customer – a guy with a lady sitting with him. But, also, only one barber. So they had to wait. Dean flicked moodily through a car magazine leaving Sam nothing to do but listen to the couple’s conversation. They sounded in almost as much trouble as Sam and Dean.

“I don’t know what else we can do, Lucy,” the guy said. He was a mousy little guy with glasses and barely enough hair left on his head to warrant a haircut. His voice was tentative.

Not so the voice of his companion. Strident, would be more the word.

“You have to _do something_ , Bill,” she said, furiously. “This job in Florida is the best paying one we’ve had for a year. This is all _your_ fault.”

“My fault?” the guy clearly felt this was such an injustice he had to speak up. “I can’t be held responsible for one of the backing singers and the sax player running off together.”

“I don’t see why they had to go. They could have had crazy monkey sex nine times a day for all I cared so long as they didn’t do it _on_ stage,” she paused for a moment, perhaps reconsidering that, but then shook herself and carried on. “We’re not that kind of show.”

“I think they were worried Barbie the Bassoonist would kill them. He used to date Candice, you know.”

Sam mulled over the use of pronouns.

“We’re never going to be able to find replacements in a town this small. There aren't a lot of transvestites in middle America…”

Ahh, right.

“… or if there are, they’re not advertising loud and proud. And even if they were, it’d be too much of a coincidence for them to be singers and sax players.”

The woman sighed loudly again – the weight of the world on her shoulders. “We’re behind already having to stop here because the bus broke down. Taking a rental coach to the station adds time _and_ money, and the train’s much more expensive than our original coach. We’re not going to be able to stop off at a city to try and recruit, or we’ll be too late and lose the job, and then we’ll have lost money on the whole thing, rather than making a tidy sum.”

The guy patted her hand. “The rental will be at the hotel by 6 and we’ll head straight off. I’m sure we can find some recruits in Florida. It’ll work out.”

Sam was wondering how on earth he’d missed a band of transvestites in a town this small when Dean jerked his jacket hard, pulling him outside.

“That’s it!” Dean said, grinning from ear to ear.

“What is?”

“We’ll escape with them. _In disguise_.”

Sam stared. There was so much wrong with that idea, he didn’t even know _where_ to start. “As transvestites?”

“Yes.”

“Transvestite musicians?”

“Yes!”

“ _Dean_!” Sam chose the simplest objection. “They’d probably want us to audition, and we’re not musicians.”

“We are! We’re so lucky, if it’d been a bassoonist… well, I don’t even know what one of those _is_ , but I can sing, and you can play the sax.”

“I _can’t_!”

“You can. I doubt they’ve got time to make us audition, but even if they did… don’t think I don’t remember you joining the band at school. You had a total geek hard-on for band camp for _years_ , but Dad wouldn’t let you go.”

“Twelve years ago! And really not to performance level.”

“C’mon, Sammy,” Dean said, slyly. “Don’t tell me you didn’t do it at Stanford with your whole embracing the normal thing. I bet you were all saxed up.”

“Maybe a little, but. Dean,” Sam took a deep breath, because honestly. Dean had to be just fucking with him. “You’re not serious.”

“I am,” Dean said mulishly.

He might be. Dean was surprisingly open minded for such a macho guy, and Sam had to confess, he’d gotten most of his sexual education from Dean (whether he’d wanted it or not. Sometimes, he’d thought his ears would start _bleeding_ ) and had received no hint of any prejudice. He remembered once they’d been waiting in the car for Dad outside a bar while Dad was shooting pool or playing poker, and Sam, eight years old, had mashed his face up against the window curiously when he’d seen two guys up against the wall, making out.

“Dean?” he’d asked. “Why are those men kissing?” Because he’d only ever seen guys kiss girls before now.

Dean had glanced up briefly from his magazine and said, “Some guys like other guys instead of girls, Sammy,” before going back to his reading. If Sam’d seen a transvestite instead, he strongly imagined he’d have been told in the same casual manner, “Some guys like dresses instead of pants, Sammy.”

So Dean wasn’t prejudiced, by any means. Universally insensitive, yes, to women, men, other races, and religions, and people with other musical preferences, but the only group of people Sam had ever known Dean to be prejudiced against were dead people, and. Well. Sam could see that.

So maybe he was serious, but, non prejudice aside, he _was_ really a very macho guy.

“So, you _really_ want to get caught in a dress?” Sam tried another tactic. “We’d never live it down. What would Henricksen say? He’d laugh his ass off. And, also? I hate to disappoint you, but they won’t send you to a women’s prison just because you were caught wearing a dress.”

Dean’s eyes glazed over a bit at that, for a moment, but he carried on. “But we’re so much less likely to get caught. Henricksen would never expect this. He thinks I’m a macho asshole.”

“Dean,” Sam said in desperation. “You _are_ a macho asshole!”

Dean grinned, “Apparently you’ve got more issues than me, liberal college boy. Shame on you.”

Sam realized it had been a mistake to be so openly – if _sanely_ – opposed to this, because his resistance had fuelled Dean’s determination, like always. He might have been only half serious at the start, but he was very serious now.

“It’s not that,” although Sam wondered uncomfortably if it might be, “it’s just that this is never going to work.”

“Rubbish, it’s got a much better chance of success than disguise by haircut and bleach. We’ll be in a group of people, which will be totally unexpected. And, hell, I’d hate to be the cop that holds _that_ woman up for long, and, you know it would make people, _aside from you_ uncomfortable and you can bet the cops won’t even be looking that hard.” Dean was downright enthusiastic now. “It’s freaking genius!”

“That woman’s totally desperate,” Dean carried on. “I bet she’d take a chance on us even if we don’t have a sax to show her you can play…”

“I _can’t_ play!”

“… because she’d only be risking room on her coach. And then. _Bam_. Home free.”

“Home free in a _dress_.” Sam mumbled, but he was starting to become slightly convinced. Madness, apparently, contagious.

Sam had one final card to play. “Dude, the coach is here at 6. That’s less than two hours away.” Sam drew himself up to his full height and spread his arms. “Where the hell am I going to find women’s clothes to fit me?”

Dean squinted up at him. “Probably best to not get high heels.”

***

Unfortunately, it wasn’t as difficult as Sam had hoped. They had a shop for the larger woman in this town, and even though they were struggling a little to get things long enough, they were certainly wide enough. And, hell, skirts could be any length, and Sam probably should wear skirts or dresses, not pants anyway, because frankly he needed all the help he could get to look like a woman.

The ladies there were really helpful. When Dean had clamped an arm around Sam’s shoulders and told them they were looking for a _lifestyle change_ , Sam had grudgingly pulled out his earnest face and sealed the deal.

They were _so brave_ , one woman gushed, and as she helped them to pick out clothes one of the others popped to the chemist to get toiletries, and Sam felt like he was in a surreal eighties movie makeover montage as the helpful ladies let them use their bathroom for hair removal (which was painful and mentally – and possibly physically – scarring, and if that Lucy woman took one look at them and laughed them out of the room, Sam was going to _kill_ Dean) and did their makeup, and explained about coloring and _flattering styles_. They’d looked rather sympathetically at Sam’s shoulders when saying that, which Sam found rather offensive.

They’d even got some wigs. Sam fingered a rather nice honey blonde one, before Dean whipped it out of his hands, saying gleefully. “With your coloring, sweetums? I think not. Best stick to brown.”

The women had nodded sagely, and then cooed over Dean who’d stuck it (somewhat haphazardly) on his head. Dean had shot him a look of triumph, while Sam could only gape.

They also cooed over Dean’s eyelashes and lips, and Sam was deeply disturbed at just how _pretty_ his big brother’s lips were with a soft, pink gloss.

“You’re going to have to shave at least four times a day,” Sam blurted out, unable to believe he’d been drawn into competing over who’d be the better woman.

Dean scowled at him in the mirror and looked, happily, a lot less feminine.

“You do have lovely skin,” one of the woman offered in apparent consolation as she applied some concoction to his face (foundation, Sam thought, noting the bottle and watching her closely – he might have to touch up on the coach, God help him). “And _fabulous_ bone structure.” She picked up some blusher, and waved it menacingly.

“And such a cute little nose,” one woman gushed, patting it with powder and making him sneeze.

They ended up looking, well, not even all that bad (so long as Sam didn’t stand up and hunched a bit). Sam looked rather striking – with his _coloring_ he could take rather more dramatic makeup than Dean – and Dean looked. Well, Sam would go with pretty, because he knew Dean had a deep and long standing hatred of the word beautiful. Sam refused to say sexy, even though he’d had to fight a worrying and deeply inappropriate erection when Dean had fluttered his eyelashes and licked his lips.

Their main problem had been shoes, but Sam had managed to find a pair that just fit in the end, and they braved the street. The ladies in the shop had helpfully informed them of which hotel the band were staying at, because some of the band members had come in to shop earlier and were apparently very chatty.

“Man, these are uncomfortable,” Dean said, glaring down at his shoes.

“You didn’t have to get ones so pointy,” Sam said

“But these are so pretty,” Dean said with a mocking grin. “… and totally the ones you wanted.”

“I did not!” Sam denied, not being secretly jealous because his shoe choices were so limited.

“Ha,” Dean said.

“I hope you get blisters.”

***

“Christ,” Dean said, “I hope this works.”

“This was _your_ idea,” Sam hissed back as they approached the hotel. “If we get caught, just let them shoot me, I don’t think I can face Henricksen.”

“Sure, Sammy,” Dean replied. “Then I’ll let them take you to the ladies’ morgue.”

The guy from the barber’s shop was outside, evidently waiting for the coach.

“You do the talking,” Sam said, pushing Dean a little bit forward.

Dean stumbled a little in his new shoes and glared back at Sam before approaching the guy.

“Excuse me, Sir?” Dean said.

“Yes?” The guy, Bill, squinted up at them and after getting a good look, looked hopeful.

Maybe this would, inconceivably, work after all.

“We understand you’re looking for a singer and a sax player?”

“Yes, that’s right.”

“Thank God,” Dean looked relieved (a little acting, a little genuine). “I hope it won’t prejudice you against us, but Candice called me. She’s a good friend of mine and she felt bad about leaving you in the lurch. We couldn’t catch you in time, but Candice found out from one of the girls that you’d had car trouble, and we hoped to catch up with you here, Bill.”

“Really!” Bill looked just as relieved as Dean. “I knew Candice wouldn’t do that to me.”

“I’m Dee and this is my sister, Samantha,” Sam expected his smile may have been more a grimace, but Bill didn’t care. “I’m a singer, and she’s a sax player.”

“Where’s your…” Bill began checking out their bags, notably short of a saxophone.

“Unfortunately, we were,” Dean looked bravely tragic, and Sam hastily assumed the same expression. “I’m afraid we were mugged on the way here, and they took Sam’s sax.” Dean patted Sam’s arm consolingly. “She’s pretty broken up about it.”

Sam blinked bravely and tragically at Bill, who gave him a melting smile.

“That must have been terrible,” Bill said. Sam nodded, looking down. Would a sniff be too much? “Never mind, dear, we’ll get you one in Florida.”

Sam smiled at him, “Thank you, Sir.”

Bill puffed himself up at that, from which clearly Sam surmised none of the others called him ‘Sir’.

“Let’s introduce you to Lucy – the manager – and the rest of the girls and get you settled, shall we?”

***

Lucy had looked at them like the second coming, not even blinking at the sax player’s lack of sax. The coach pulled up, and they were introduced to the others.

Mostly, they complimented their makeup and Dean’s shoes (damn him) and asked after Candice. Dean was in his fucking element, comfortable anywhere, and made up wild stories about being mugged, and Candice’s weeping remorse at leaving them. Sam hoped to avoid the bassoonist for the trip, or else Dean might find even his story telling stretched. He was interrupted, probably just before Candice’s suicide attempt, by the arrival of the final band member, and lead singer, Sugar Kane.

“Welcome, honeys,” she said as she tripped past to the coach, clad in high heels, and a sweater and skirt that redefined _tight_ , platinum blonde hair bouncing, along with _everything else_.

“Holy crap,” Dean said, eyes nearly bugging out and voice dropping out of the register he’d been using to tell his tall tales. “That is un-be-freaking-leivable.”

Sam would have rolled his eyes, but he was too busy watching Sugar because, Dean? Had a point.

“Oh,” one of the girls, Traci, laughed. “You didn’t know? She’s the only real live girl in the band. You know the name? Sugar Kane and the Sweeteners? Because she’s real and we’re not quite?” She winked. “Just as good, though. Better!”

“Oh thank God,” Dean said, eyes glued to Sugar’s behind as she went up the stairs.

The others all headed off to the coach while Sam and Dean finished talking to Bill and Lucy. Bill mainly reassuring Sam that they’d get _her_ a new sax just as soon as they could and patting Sam’s arm consolingly. Sam was rather disturbed.

“Dee?” Sam said as they headed off towards the coach, following Lucy and Bill. “Dee? _Dean_?” a hissed whisper and Dean turned. “Do _not_ hit on Sugar. Do you hear me? Getting us thrown off the coach would be suicide.”

“Sure Sammy,” Dean said, not at all convincingly.

Sam deliberately got on the coach first, which was good thinking as it turned out, because as luck would have it there were no free double seats together and a free one next to Sugar which Sam took, quickly. Dean kicked him as he went past.

“Be good, Dee,” Sam said, sweetly.

Sugar smiled at him.

“Where are you from?” she asked.

“Oh, all over,” Sam replied. “My, er, sister and I. We go where the job takes us.”

“Me too,” Sugar smiled. “I’m from Idaho originally, but I’ve been all over. Traveling towards this or away from that.” She smiled again, and was even more beautiful. “Mostly away.”

Sam looked sympathetic.

“Were you running away from something with this band?” he asked, feeling the coach pull away. His heart beat faster as they approached the roadblock. This could be the shortest trip in history.

“A guy,” Sugar said, with a small laugh. “What else?”

“Oh yeah?” Sam encouraged.

“A real heel. Told me he loved me, took me for a ride and dropped me flat,” she said, pouting. “Same old story.”

“I’m sorry Sugar,” he said. “Maybe you’ll meet a nice guy in Florida?”

“That’s what I’m hoping,” she said with a smile. “A nice _rich_ guy who’ll take care of _me_ for a change.”

“Good thinking,” Sam slumped down in his seat as a cop passed – looking in the window. He should have sat next to someone taller.

“Are you alright?” Sugar asked, looking concerned.

“What? Oh, yes. Just, uh, felt a little faint. I’ve, uh, been on a diet. I’m a bit big, you know,” he smiled depreciatingly.

“Oh I _know_ , sweetie,” Sugar said, grasping his hand. “I’m on a diet myself.”

“You are?” Sam asked, surprised. He couldn’t imagine how Sugar’s figure could _get_ any better. Dean had been practically drooling.

“My last boyfriend called me fat.”

“He _did_?” Sam asked, even more surprised.

“That’s one of the reason’s I chose this band – it’s too dangerous to be in a band with men… I’m a sucker for a sax player,” Sam smiled at that, “but I can’t be in a band with other women. They make me feel fat.”

“Christ!” Sam said. “That’s unbelievable.”

“You’re kind sweetie,” she said, smiling. “Most of this band is envious of my boobs,” she said, bluntly, “but anyone can get implants now and so be chesty and extra skinny elsewhere.” She brightened up. “At least mine are all me.” She winked and shimmied a little in her seat.

“Yes,” Sam said, a little hoarsely. “I see.”

And so Sam had been more pleasantly engaged as the coach passed through the roadblock without their pursuers even looking inside. Dean had been right, both thankfully and annoyingly. The cops hadn’t wanted to get on a bus with a group of transvestites, probably more from embarrassment than prejudice, but for whatever reason, Sam was appropriately grateful.

As soon as they got to the station he was finding a restroom and reclaiming his manhood, before getting a ticket to South Dakota and Bobby’s sanity.

He spent the trip to the station chatting with Sugar – who was lovely – and hating his bra.

***

“Dude,” Dean said, grinning as they disembarked from the coach. “I’m a freaking genius.”

“And I’m fed up of pantyhose,” Sam said, not acknowledging Dean’s rightness. “Let’s get going.”

“No, wait,” Dean said, eyes on Sugar. “I’ve had a better idea.”

“Oh?”

“We’ll go to Florida. One of the hunts we were looking at doing next was in Florida, wasn’t it?”

“You are _not_ serious.”

“No, really. You won’t believe it, but Traci said we’re staying at the Blue Mermaid Hotel. That was one of the ones mentioned in the article, wasn’t it?”

“You’ve lost your mind.”

“We could go, take care of business and come back in time to meet Bobby and pick up the Impala, instead of wasting time. Lives need saving, Sammy.”

“You’re fooling no one, Dean,” Sam said, moving to block Dean’s view of Sugar. “You want to stay for Sugar.”

“Dude,” Dean said with a grin, giving up the pretense. “That’s worth wearing pantyhose for.”

“Get a grip, Dean. If we go, I’m going to be expected to _play_ the saxophone, and I’m really not up to it.”

“I think Bill would keep you even if you couldn’t play a note,” Dean said, with a grin. “C’mon Sam, let’s go to the beach.”

“Fine,” Sam said, with a sigh. “But don’t blame me if you develop a taste for women’s underwear.”

***

Dean spent the train journey making conversation with Sugar and stealing a particularly large lady’s luggage because while they had toiletries – they’d had to buy them, of course – they only had one set of clothes each.

Dean attempted to feel out what Sugar was looking for in a man. Sam could have helped him out there. _Not a love ‘em and leave ‘em type_ and _rich_. Dean was pretty much out of luck there on both counts.

She wanted a sensitive man, refined – and Sam snorted at that, earning a kick under the table for his trouble.

***

They took a large coach from the station to the hotel, and Sam couldn’t beat Dean to the seat next to Sugar. When they arrived Dean rushed ahead with Sugar and left Sam with the bags, including Sugar’s. As Sam was struggling in, a guy came up and walked next to him.

“So, you’re with the band,” he said. “You playing tonight?”

“God, I hope not,” Sam muttered.

“What time do you finish?”

Sam stopped and stared at the guy. Was he trying to pick him up? The guy was definitely checking him out.

“You know I’m a guy, right.”

The guy squinted up at him. He was dirty blonde and good looking in a scruffy sort of way. “Uh. Yes.” The duh was strongly implied. Obviously, Sam’s makeup wasn’t working as well as he’d hoped.

“Okay then.” Sam struggled to the elevator. The guy didn’t offer to help but followed him there.

“Well,” Sam said, getting in. “Thanks for your help.”

“I’ll see you after the show.”

“Great.” Sam muttered as the door closed. “Look forward to it.”

***

Sam and Dean had been assigned a room to share, which made research that much easier. Bill had produced a saxophone and some music which fortunately Dean already knew the words to. Sam therefore made Dean do the research, much to his annoyance, while he furiously practiced the sax. He wouldn’t play too loudly, and there should be enough other music to cover his mistakes. There was happily no sax solo, and Sam practiced hard on the parts where the sax was a stronger player, hoping to blend in the rest of the time. Fortunately they weren’t playing that night – the band allowed one evening to settle in – so Sam did, at least, have time to practice.

“People are going missing off boats.” Dean summarized the case over Sam’s music (if music wasn’t too generous a description.) “It’s been small mostly. A guy in a dinghy out fishing, a small rented boat with a young couple who were staying at this hotel, and last week four people went missing off a boat.” Dean squinted miserably at the laptop, he hated researching. Ha, Sam thought, licking his already slightly swollen lips, they could both be fucking miserable. “In all cases no bad weather reports. No bodies recovered, and the boats found intact. Official line is they went swimming and got swept away, but the first guy’s wife reckons no way he goes swimming, and anyway, people swim in these waters all the time. The current’s not strong.

“There doesn’t seem to be any connection between the victims – different ages, different lifestyles, but we can check that with the relatives. The only link so far is they were all on boats out on the sea at about midnight.” Dean snapped the laptop shut. “That’s it. I guess we’ll have to rent a boat and head on out there with as many weapons as we can.”

Sam put the sax down and stretched, back aching and throat parched from the practicing. _Get me some water,_ he thought fiercely at Dean.

Dean got up and straightened his wig.

“I’m going to see if Sugar wants to get a drink,” Dean winked at him. “Practice hard, Sammy.”

Sam sighed as he watched Dean leave, and got up to get some water from the bathroom. Such a pity his mind-mojo only worked in life-or-death situations. When it came to Dean’s life, his _soul_ , Sam could whammy a demon into walking into a Devil’s Trap. When it came to a refreshing beverage, he was apparently on his own.

***

The next day, Sugar and the other girls invited Sam and Dean to the beach, but while Sam greatly admired transvestites who were prepared to wear swimming costumes, he didn’t feel he was quite ready for that.

Also, he needed to practice.

Dean went off to interview the victims’ relatives, leaving Sam in peace.

After too many hours, though, Sam needed a break and so went down to the hotel bar for a drink and some food.

The guy from last night appeared in the seat at his table.

“You didn’t play last night.”

“No,” Sam replied.

“Are you playing tonight?”

“Do you have a music fetish?” Sam asked.

“No,” the guy answered, seemingly a little confused by the question.

Sam pointedly returned to his sandwich.

The guy shifted a little in his seat. Sam had the impression he wasn’t very good at small talk.

“What’s your name?”

Sam sighed. “Sam.” If he started talking about the weather, Sam was taking his sandwich upstairs.

“I’m Chad.”

“Great.”

“Will you meet me after the show?” So much for small talk.

“I don’t think so.”

“We can go out to my yacht. Have some dinner…”

“You have a yacht?”

“…fuck all night.”

Sam looked at him. “Your chat up lines could use some work.”

Chad shrugged, not at all offended. “I’ve been married five times. I don’t do so bad.”

“It’s probably your yacht.”

“Probably.”

Sam sighed. A yacht was bigger and probably therefore safer than renting a smaller boat to investigate the disappearances.

“Fine. I’ll meet you after the show. But _only_ for the first two.”

“Huh?”

“Just a trip to the yacht and dinner. No…”

“Fucking all night?” Chad looked disappointed.

“No.”

“OK. I’ll pick you up here and then we’ll go from the dock in the speedboat,” Chad shrugged like a man used to disappointment. He got up. “Oh,” he turned back and chucked a small box at Sam, which Sam caught automatically. “Got you this.”

Sam opened it as Chad walked away and found a diamond bracelet inside.

“Christ.”

Sam looked up and saw Chad passing a couple on the steps of the hotel. One was Sugar and one was…

“Dean.” That slacking horndog. Dressed in… where the hell had he gotten that suit? And glasses? And, hey, was that Sam’s copy of _Catcher in the Rye_ in Dean’s pocket?

Dean gave Sugar a final chaste kiss on the cheek and then on the hand, waving at her as she came back through the hotel doors.

Dean met Sam’s gaze over Sugar’s head and grinned happily at him, giving him the thumbs up. Sam sighed, and shot disapproval at him. Water off a duck’s back, sadly, though, and Dean waved at him cheerfully before disappearing, presumably to go up the fire escape.

“Sam!” Sugar said gleefully, grasping his hands. “You won’t believe it! I met a guy. He’s handsome, _gorgeous_ , smart, sensitive. He wears _glasses_!” Sugar hugged him. “I met a billionaire!”

“So did I,” Sam said. “A _rich_ billionaire.”

“Really! Fantastic! Uh, what?” Sugar asked, frowning.

“Never mind.”

“He’s meeting me after the show tonight for dinner and dancing.”

“I’m going on his yacht,” Sam said, meanly.

“Ohh,” Sugar said, linking hands with Sam and leading them upstairs. “I wonder if Junior’s got a yacht?”

“Junior?” Sam stifled a smirk. _Right now he hasn’t even got a car._

***

Dean was grinning when Sam came in.

“So what are you this time? A movie producer? Reality TV mogul? Oil baron?”

“Nah. Old money.” Dean grinned harder.

“Jerk.”

“I’ve got us a boat,” Sam said. “You find out any information before you went looking for Sugar?”

“Nothing concrete, but maybe. The first guy’s wife showed me the route he always took fishing, and the rental guy showed me where most people go. Both routes happened to meet round about where the last group moored their boat.”

“Great,” Sam said. “I’m meeting a guy with a yacht tonight. I’ll make him take me there and sort it out.”

“Tonight?” Dean whined. “Does it have to be? I’ve got a date with Sugar.”

“ _Junior’s_ got a date with Sugar and, yes, it has to be tonight. That’s when I’m meeting him and we don’t want any more disappearances. And anyway, the sooner I get this done, the sooner I’m on a train in jeans and a hoodie.”

“Damn,” Dean sulked.

“You don’t have to come.”

“Right.” Dean said. “That’ll happen.”

Sam smiled. “This’ll make you feel better.” He threw the box with the bracelet in to Dean.

“Whoa.”

“Yeah,” Sam said. “It’s good to know if this hunting thing doesn’t pan out I’ve apparently got a great future as a _cross-dressing hooker_.”

Dean half smirked, but half frowned.

“What’d you let him do for this?”

Sam raised his eyebrows. “Take me to dinner on his yacht. What the hell do you think?”

Dean shook it off, “Nothing. Just I’ve been keeping you by playing pool and poker for years, and you never put out for me.”

“Bite me.”

“What are we gonna do with the guy while we’re on his yacht anyway?”

“I’ll let him take me out there and then slip him a roofie. You can stow away in the speedboat with the weapons, then we take care of this thing.”

“Sounds like a plan. Dress real pretty, Sammy, you don’t want him to change his mind.”

***

Dean sent Sugar some roses as an apology, which was unusually thoughtful of him and made her happy.

Shockingly enough, the performance wasn’t too bad, that evening. For the most part, Sam fumbled his way through, and did pretty well when the sax was required to take a stronger role. Dean, frankly, was apparently born to perform, singing away with Traci, the other backing singer, behind Sugar, winking and blowing kisses to the crowd. Dean had a really nice voice, (and also lips) but Sam would never admit either of those, on pain of death.

Chad was there and Sam smiled awkwardly at him as he met him after the performance. Chad’s small talk hadn’t improved, but, bearing in mind Sam was about to drug the guy and feeling a little bad about it, Sam held up his end.

“Which is it?” Sam asked as the speedboats came into sight.

“That one,” Chad pointed to a black and gold speedboat with _Mayhem_ written nice and sparkly on the side. Great, a pimpmobile.

Sighing, Sam pulled Chad’s attention back to him, in order to give Dean a chance to slip on board. “It’s lovely,” he said, keeping the sarcasm out of his voice, and in the event of failing inspiration, he pulled Chad in for a kiss.

Chad was clearly surprised, but not as surprised as Dean, who stopped in the middle of his stealth run to the speedboat to gape.

Sam grinned against Chad’s lips and made a _hurry up_ gesture behind his back. Dean shook himself and carried on.

The kiss wasn’t unpleasant. Chad was enthusiastic and tasted of salt, smoke and mint. Not all that different from kissing a girl actually, although beard burn was odd. He’d have to be more considerate in the future.

When he was certain Dean was in, he let go.

Chad look dazed and then grinned. It transformed his whole face. “Wait until you see the _yacht_.”

Sam laughed.

The yacht, if not decorated in Chad’s execrable taste, would have been nice – spacious and well equipped. Sam quickly got his bearings from his and Dean’s earlier research.

“Could we go over there?” Sam asked, pointing to roughly where the disappearances were thought to have taken place. Chad frowned. “The, uh, moon will look more romantic over there.”

Chad didn’t appear to have heard Dean’s muffled snort from underneath the lifeboat.

“I suppose,” Chad shrugged. “Give me a minute. I usually have staff to sail it, but I gave them the night off.”

“I told you I’m not that kind of girl,” Sam said automatically, but he kicked himself for not thinking there might have been staff.

They moved over to where Sam thought the action would be and then Sam let Chad take him into a room where there was a couch, pizza and beer, and a large screen TV.

Sam laughed, “You are a master seducer.”

“Thanks.”

Sam slipped a mickey into Chad’s drink while he turned on the TV.

It was football, but Chad didn’t seem particularly interested in that – more interested in getting into Sam’s panties.

“Chad!” Sam slapped his hand away from his thigh, primly. “I told you, I’m not that kind of girl.”

“Got to try,” Chad said with a grin that was becoming slightly glassy.

Sam patted his hand. “Have some more beer.”

Sam glanced up and saw Dean’s face at the window. He smiled.

“Maybe some more beer will help me to relax too.”

He shifted a little closer to Chad and let him kiss him.

“You’re so pretty,” Chad said against his lips.

Sam smirked. He could see Dean’s eyes bugging out at the window, and he let Chad’s hand rest on his knee, and slide up a few inches.

Happily, Sam’s leg was extremely long, and Chad didn’t get much further, because with one more whispered, _pretty,_ Chad slumped forward, unconscious.

Sam pushed him off gently and Dean burst in.

“I can’t believe you let him kiss you! That, that, _pig_.”

Sam snorted.

“And he was. He was. Touching you!” Dean continued, staring at Chad with something like rage. Sam took a moment to be grateful he hadn’t been Dean’s baby _sister_ , because he clearly wouldn’t have been allowed to talk to the opposite sex until he was 21. Maybe not even then.

“I was in the moment,” Sam said, breezily, smoothing down his skirt.

Dean spluttered in outrage.

“C’mon, let’s see if we can find this whatever it is,” Sam pushed past Dean, annoyed to see that Dean had taken the opportunity to change into jeans and a t-shirt. It sucked to be the only one in a skirt.

They peered over the side of the boat, weapons in hand. It was going to be pretty annoying if nothing happened… he doubted even Chad would let himself get roofied two nights in a row. They’d have to rent a boat and…

“Shit!” Sam jerked forward as something surged out of the water and grabbed him, almost pulling him overboard. He dropped his gun in shock as long, cold fingers gripped his arms tightly. Dean grabbed him, pulling back hard, but it wasn’t quite enough and they were caught there in a bizarre tableau with a Grindylow hanging off him, dangling a few feet above the water, and Dean trying to pull him back.

Grindylow’s were green, man-sized water demons with long fingers and sharp teeth which pulled the unwary into water, grabbing them from the shore if they got too close and even off boats, if they crossed over their lairs. It looked like the Grindylow had just moved in and hadn’t taken kindly to the neighbors. Alas, unlike in Harry Potter lore, a Grindylow’s grip was almost impossible to break – kill it or lose whatever it’s holding on to. A second Grindylow leapt out of the water, climbing up the yacht’s side, heading for Dean.

There was no way Dean would release Sam to defend himself, and Dean had dropped his gun, too.

“ _Let go_ ” Sam yelled with all the power he could muster at the Grindylow attached to his arms.

It let go and looked comically surprised as it fell back, flailing, into the water.

Sam tumbled back at the sudden release, landing heavily on Dean. The second Grindylow shrieked and launched itself at them. They rolled out of the way, scrambling for the weapons they’d dropped. Dean shot the Grindylow on deck just as it reached for him, and Sam plugged the other one as it leapt back over the side.

They fell back, panting.

“Fuck,” Sam said, looking down at his sleeves. “It totally ruined my blouse.”

***

They tossed the Grindylows back overboard, weighted down by some fugly lamps that probably cost a fortune, and then they went searching for Chad’s bedroom to find a shirt.

Sam pulled off his blouse and rifled through Chad’s closet in his bra. He could really lose the bra now, he thought, but he was probably going to have to keep the skirt – there was no way any of Chad’s pants would fit him.

He was surprised when Dean appeared next to him with some antiseptic cream, clearly swiped from Chad’s en suite, and pulled at Sam’s hands to get access to the bruises already rising on Sam’s arms where the Grindylow’s epically strong fingers had grasped tight.

Dean’s face was stormy. His mood was always black after Sam had been in danger.

“Fucking things,” he muttered, almost under his breath, applying the cream with surprising gentleness to the bruises. “Fucking touching you. Fucking Grindylows _touching_ you. Fucking _Chad_ touching you.”

Sam raised an eyebrow. “I could handle Chad.”

“Yeah but you _weren’t_. Fucking _letting_ him touch you. Bastard.”

“Jealous much?” Sam asked, mocking.

Dean’s fingers froze for a minute on Sam’s wrist before moving again. “Nah, just didn’t realize you were into that sort of thing.”

“I was just fucking with you,” Sam said, after a long moment.

Dean grunted and didn’t look up from where he was still gently tending to Sam’s wrists.

Sam took a risk.

“But maybe I was trying to make you a little bit jealous,” Sam paused. “Maybe?”

Dean looked up, eyes dark, but with a slight grin. “Good job.”

Sam grinned in relief.

“So what are you gonna do about it?” Sam asked.

Dean paused for a moment, weighing him up before smiling wickedly.

“Pretty much gonna touch you everywhere you let him touch you. And where you _didn’t_.” Dean was very much a man of action when a decision was made.

Sam laughed. “Good plan.”

“Starting right here,” Dean said, and rubbed his fingers over Sam’s lips. He half grinned. “Gonna mess your lipstick all up.”

Dean pulled his head down and kissed him, hot and hard, and still, maybe, a little bit pissed. Kissing Chad had been a lot like kissing a girl. Kissing Dean wasn’t like kissing anyone else. Ever.

Sam moaned softly as Dean licked into his mouth, demanding but careful, gently touching his face, before pulling back.

“Fucking touching you,” he muttered, clearly still not over that. “Not fucking touching you again.”

He pulled Sam over to the bed, grinning suddenly. “I’m fucking touching you _on his bed_. Hah.”

“Very mature,” Sam said with a grin, but he laid back on the bed, letting Dean lean over him.

Dean slipped a hand up Sam’s thigh. “Christ Sammy, your legs are smooth. And _long_.”

Sam sucked gently at Dean’s neck, before pulling Dean’s shirt over his head.

“C’mon,” Sam said, smoothing his hands down Dean’s chest. “C’mon, Dean.”

Dean pulled off Sam’s bra, clearly a practiced maneuver, and pinched his nipple.

“Shit!” Sam arched off the bed.

Dean grinned evilly, and bent over to suck it.

“Oh holy fucking Christ,” Sam moaned as Dean sucked and bit and licked.

He pulled back, and blew over the swollen, reddened flesh, before switching to the other. Sam’s dick throbbed.

“Dean, fuck, Dean.”

“Want me to suck you, Sammy?” He asked, licking his pink lips and grinning.

“Oh, fuck,” Sam said, hips jerking off the bed. “Get the fuck on with it before it’s too late.”

Dean grinned and pushed up Sam’s skirt.

“Oh my God,” Dean breathed. “You’re wearing _panties_.”

“I had to!” Sam said defensively. “What if my skirt pushed up and Chad had seen boxers under there?”

“Yeah, right, Sammy. I know you just like it.”

But Dean really wasn’t complaining, apparently. He reached down to cup a big warm hand over Sam’s cock, which was straining hard and leaking inside his pink cotton panties, wetting the front.

“All nice and wet like a girl, Sammy,” Dean grinned, squeezing.

Sam’s eyes rolled back in his head, but he managed to say, “That feel like a girl?” as he pumped up into Dean’s hand. “Shut up and suck me already.”

“So impatient Sammy,” Dean mocked. “Thought you were the one with self control.”

But he bent down, pushing Sam’s thighs apart, and put his lips on him, mouthing him, sucking, through the cotton.

“Fuck,” Sam groaned, vocabulary out the window. “Oh fuck oh fuck. _Dean_.”

Dean hummed against Sam’s cock, and Sam pulled Dean’s head back in a hurry.

“Dean, c’mon. Do it, please. I want your lips around me. Such fucking pretty lips.”

Dean grinned up at him, licking them provocatively.

“Fuck, Dean, they were so pretty in that lip gloss - all pink, and slick and shiny.”

Dean laughed. “Maybe I’ll wear it again for you sometime. Leave a lipstick ring around your dick. But for now I’m just gonna pull your panties down and suck your cock, quick and dirty.”

Sam’s eyes were glued to the sight of Dean pulling his panties down his thighs and bending down to take Sam’s cock between those perfect lips. Oh, fuck, so soft and wet and hot, and Sam’s eyes wanted to close, but he couldn’t fucking miss this.

Dean sucked tightly at the head, making wet, dirty noises, and Sam couldn’t help it, he bucked up at the sight of Dean’s pretty mouth stretched wide around his cock.

Dean rode his thrust, gripping the base of Sam’s dick that he couldn’t get in his mouth and jacked him hard and tight as he dragged his lips tight and smooth up and down Sam’s cock.

Sam couldn’t last.

“Fuck, Dean, I’m gonna come.”

Dean hummed around him and sucked harder, and that was all she wrote, Sam came in Dean’s mouth.

“Christ.” Sam fell back, boneless against the bed.

“Good?” Dean asked, grinning wickedly. He opened his fly and pulled his dick out, and his eyes were glued to Sam. Sam lay sprawled and sated with his skirt up around his waist and his panties round his thighs as Dean grasped his own dick.

Sam realized he was going to jerk off.

“Don’t you want to fuck me?” he asked.

“Fuck,” Dean gripped his dick, hard. “Fuck. You’d let me?”

“See if Chad’s got anything,” Sam jerked his head towards the bedside cabinet.

Dean dived for it with amusing eagerness and emerged triumphant with a strip of condoms and a bottle of lube. Then he scowled again.

“Fucking bastard better not have thought _he_ was using these on you.”

Sam rolled his eyes, but didn’t argue, because he wanted Dean back on track.

“Wanna fuck me in my skirt?”

“Oh, fuck, yes.”

Dean hurriedly pushed his jeans and shorts further down and pulled the condom on, slicking lube over himself.

“You done this before?” Sam asked.

Dean paused.

“Come on, I know you’ve sucked cock before. No one’s that good first time.”

Dean puffed up under the praise. “Couple of times. You?”

“Not from this side,” Sam said, refraining from admitting that on the other side it had been with a woman, not with a man. Another time. Dean might baulk if he knew he was Sam’s first guy. “So go slow.”

The glee on Dean’s face was practically blinding.

“I’m gonna be the first,” he crowed, happily. Or, he might think it was the best thing ever.

“Only if you hurry up,” Sam said. “Otherwise I’m gonna go and try and wake Chad.”

“Bitch,” Dean said. “Roll over.”

Sam grinned and turned over. He looked back. “Gonna do me on my belly, or you want me on my hands and knees?”

“Hands and knees,” Dean said hoarsely. “Wanna _see_.”

Sam pushed himself up and put his ass in the air for Dean. Dean groaned and moved immediately behind Sam, parting his thighs as far apart as they’d go with his panties still around his knees.

“So fucking perfect,” Dean said, and Sam felt a soft kiss land on his cheek. Before he could say anything, though, it was replaced with a hot hand and Sam felt a slick finger at his asshole.

He was still relaxed and loose from his orgasm, so the finger slipped in easy.

“God you feel so hot, so tight, Sammy,” Dean whispered against his back where he’d rested his forehead. “Gonna feel so good inside you.”

Sam relaxed as another finger slid in.

“How’s that feel, Sammy? S’good?” Dean sounded almost drunk.

“Yeah, it’s good, Dean. C’mon,” Sam encouraged him, softly.

Dean kissed his back as he put in a third finger, stretching, rubbing up, searching gently and pushing against Sam’s prostate. “Fuck,” Sam groaned, half-hard cock springing up all the way. “Yeah, Dean, that’s it.”

Dean scissored his fingers in and out, thoroughly slicking and stretching Sam, fucking him open, ready for Dean’s cock.

“Now, Dean,” Sam said, voice harsh and broken. “Need you now, Dean.”

Sam felt Dean’s cock hard and _so hot_ slick against his ass pushing in gently.

Sam groaned and let his head fall down as he was stretched so wide. Dean felt fucking huge inside him, burning painfully, felt like he was splitting him open.

“Sam,” Dean groaned. “Oh fuck, Sam.”

Sam breathed hard, letting Dean in until he felt Dean flush against him. Dean remained still, seated deep in Sam’s ass, mouthing softly at Sam’s back between his shoulder blades. Sam couldn’t quite hear all the words Dean was murmuring, muffled as they were against his skin, but they were soft and broken, and Sam caught _mine_ , and _always_ and _love_ and _Sammy_.

It didn’t seem like Dean was ever going to move, content to just stay there deep inside Sam, but Sam wanted more and rocked his hips back, squeezing down on Dean.

Dean gasped and jerked his hips forward with a strangled curse.

Sam saw stars and groaned.

“Come on, Dean. Come on, do it.”

Dean thrust in and out, fucking him gently at first and then, faster and harder. It felt so good. So fucking good.

Dean bit down hard on his shoulder, and that was it for Sam. He came again, hot and hard into air as Dean fucked him hard and deep.

Sam dropped his face down into the pillow, his ass in the air, and felt every inch, every thrust of Dean fucking his ass, heard the choked off noises and words, and the sobbed out _Sammy_ as Dean came deep inside him.

Dean collapsed onto Sam before pulling out gently and rolling off, burying his face in the pillow.

Sam left a hand on Dean’s shivering back, softly stroking while he let Dean recover.

“Dude,” Dean said hoarsely after a while, turning to look at Sam, all traces of sentiment wiped off his face. “You’re such a slutty girl. You let me fuck you with your panties still round your knees.”

Sam flipped him the bird, pulled up said panties and tugged down his skirt.

“Yeah, loverboy, next time see if you can get your jeans all the way off.”

They got out of bed. Sam felt a little guilty at the state of Chad’s sheets, but, hey, he didn’t really imagine Chad would mind.

“Let’s get back,” he said. “And we’re leaving tomorrow. No Sugar for you. You’re on a strict diet from now on.”

“Yeah?”

“Oh yeah.”

***

Dean was off stealing a car while Sam waited to be picked up at the hotel. This was definitely his last day in a dress. Hallelujah! They weren’t leaving as early as they’d meant to, because Dean wanted to take full advantage of the last day of easy access and Sam had let him suck him off and then fuck him against the wall. He still hadn’t managed to get his panties all the way off, dammit.

Sugar sat next to him, looking a little depressed.

“Junior never called,” she said, sadly.

“I’m sorry, Sugar,” Sam said, patting her hand. “But I don’t think he was right for you, anyway. There’s a _rich_ billionaire out there for you somewhere.”

Dean pulled up on the road and honked.

“Anyway, we’d better go.”

Sugar hugged him, “I’m sorry you’re leaving.” She waved at Dean. “Bye Dee.” She called. Dean waved back looking a little sheepish.

As Sam made his way down the long path, he felt a hand on his shoulder. He turned around. Chad.

“Hi Chad,” he said; his turn for sheepish.

“You drugged me!” Chad accused.

“Sorry.”

“Did you take advantage of me?” Chad asked hopefully.

Sam shook his head. “Sorry.” Chad looked crestfallen.

“Look, my boyfriend and I,” (Dean would never know) “used your yacht and your, uh, bed. I’m sorry. Do you want your bracelet back?”

“Nah, keep it,” Chad sighed.

Sam patted his shoulder, and then with a sly look at the car where Dean was waiting, kissed his cheek.

“Bye Chad.”

“See ya.”

“Hey,” Sam said, “you see that girl up there?” He pointed towards Sugar.

“The band’s lead singer?”

“Maybe you could buy her a drink.”

Chad slouched off. Hey, he might not be sensitive or educated, but he was, at least, a genuine billionaire, and, well, quite a sweet guy under the complete lack of social graces.

He reached the car and met Dean’s furious gaze with a smile. Maybe there’d be one more chance to take advantage of the skirt’s ‘easy access’.

***

As they drove away, they passed Sugar and Chad, and Sam caught a snatch of their conversation.

“You know I’m a girl, right?”

Chad shrugged. “Nobody’s perfect.”

***

**Author's Note:**

> Comments are lovely, and if you’d like to comment please feel free to do so here or on [this fic at livejournal where it was originally posted ](http://jasmasson.livejournal.com/53509.html) as you prefer.


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